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Reducibly degradable amphiphilic block copolymer and preparation and application of amphiphilic block copolymer used as drug carrier

An amphiphilic block and copolymer technology, applied in the fields of polymer chemistry and biomedicine, can solve problems such as toxic and side effects, reducing the effect of drugs on the target site, and increasing the drug resistance of tumor cells.

Inactive Publication Date: 2014-07-16
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, polymer nano-drug carriers also have shortcomings. Too fast release of the drug before reaching the tumor site can lead to toxic side effects and reduce the drug concentration at the target site; too slow release will reduce the effect of the drug on the target site and increase the number of tumor cells. Therefore, the controlled release of the drug from the drug carrier becomes the key point of this drug delivery system

Method used

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  • Reducibly degradable amphiphilic block copolymer and preparation and application of amphiphilic block copolymer used as drug carrier
  • Reducibly degradable amphiphilic block copolymer and preparation and application of amphiphilic block copolymer used as drug carrier
  • Reducibly degradable amphiphilic block copolymer and preparation and application of amphiphilic block copolymer used as drug carrier

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] (1) Preparation of disulfide bond monomer: Weigh 1.54 g (10 mmol) of 2,2-dithioethanol, dissolve it in a round-bottomed flask with 10 mL of THF, and place it in an ice-water bath. Add 3 mL of triethylamine (20 mmol) dropwise to the round bottom flask and stir for 20 min. Dissolve 0.5 mL of freshly prepared methacryloyl chloride (4.8 mmol) in 5 mL of THF and slowly add it dropwise to the above reaction flask. After the dropwise addition was completed, it was stirred in an ice-water bath for 2 h, and left at room temperature overnight. After removing the solid product by filtration. After the THF was removed by vacuum rotary evaporation, 50 mL of dichloride was added to dissolve the solid product, and the filtrate was washed with dilute hydrochloric acid solution (mass concentration 2%), sodium bicarbonate solution (mass concentration 2%), high-purity water, and dried over anhydrous magnesium sulfate. Layer, 0.58 g of disulfide bond monomer compound was obtained with a ...

Embodiment 2

[0047] (1) Preparation of disulfide bond monomer: same as Example 1;

[0048] (2) Preparation of grafted Rhodamine B disulfide bond monomer: same as Example 1;

[0049] (3) Preparation of intermediate interpolymer: same as Example 1;

[0050] (4) Preparation of the target copolymer: Weigh 0.050 g of the intermediate copolymer, 0.329 g (2.30 mmol, 96.6%) N-(2-hydroxypropyl)methacrylamide (HPMA), put it in a Shleck bottle, and use Dissolve 2 mL of DMSO; add 0.0189 g (5%, wt) azobisisobutyronitrile (AIBN), vacuumize and inflate with nitrogen for 3 to 5 times, seal and keep the temperature at about 55°C for 24 h. Precipitate with petroleum ether, centrifuge with an ultrafiltration concentration centrifuge tube with a molecular weight of 3000, remove small molecules, and obtain 0.130 g of polymer with a yield of about 34.3%. Mn=1.45×10 4 , Mw / Mn=1.37. 1 H NMR (400 MHz, DMSO, δ, ppm): 8.41- 6.84 (Ar), 3.65 (CH 3 C H (OH)CH2 NH- of HPMA and -N(C H 2 CH 3 ) 2 ), 2.89 (CH 3 ...

Embodiment 3

[0053] (1) Preparation of disulfide bond monomer: same as Example 1;

[0054] (2) Preparation of grafted Rhodamine B disulfide bond monomer: same as Example 1;

[0055] (3) Preparation of intermediate interpolymer: same as Example 1;

[0056] (4) Preparation of the target copolymer: Weigh 0.025 g of the intermediate copolymer, 0.128 g (0.89 mmol, 95.7%) N-(2-hydroxypropyl)methacrylamide (HPMA), put it in a Shleck bottle, and use Dissolve 2 mL of DMSO; add 0.0122 g (8%, wt) of azobisisobutyronitrile (AIBN), vacuumize and inflate with nitrogen for 3 to 5 times, keep the temperature at about 55°C after sealing, and react for 24 h. Precipitate with petroleum ether, centrifuge with an ultrafiltration concentration centrifuge tube with a molecular weight of 3000, remove small molecules, and obtain 65 mg of polymer with a yield of about 42.4%. Mn=1.30×10 4 , Mw / Mn=1.25. 1 H NMR (400 MHz, DMSO, δ, ppm): 8.46- 6.85 (Ar), 3.62 (CH 3 C H (OH)CH 2 NH- of HPMA and -N(C H 2 CH 3 )...

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Abstract

The invention provides a preparation method of a reducibly degradable amphiphilic block copolymer used as a drug carrier, and belongs to the technical field of macromolecular chemical and biological medicines. The method comprises a step of bonding rhodamine B serving as a fluorescent agent to a disulfide bond monomer through esterification, and bonding to N-(2-hydroxypropyl) methacrylamide in a RAFT mode to form the amphiphilic block copolymer with high biocompatibility. According to the amphiphilic block copolymer, a nano-micelle drug carrier can be formed in a mixed solution of methanol and water. In a reducing environment, the disulfide bond in a hydrophobic chain segment of the amphiphilic block copolymer can be reduced into a sulfydryl group, and the grafted rhodamine B group is removed out of the side chain of the polymer to result in reduction of the grain size of micelle and obvious change of the structural properties of the drug carrier, so that the amphiphilic block copolymer shows high reducibility, degradability and drug release property; therefore, the amphiphilic block copolymer can be used as the drug carrier to be applied to preparation of medicines.

Description

technical field [0001] The invention provides a reductively degradable amphiphilic block copolymer, belonging to the technical fields of polymer chemistry and biomedicine. The invention also relates to the application of the copolymer as a drug carrier. Background technique [0002] In the past few decades, research on polymer systems for drug delivery and gene delivery has developed rapidly. Especially based on amphiphilic block copolymer self-assembled drug carrier, which is composed of hydrophilic shell and hydrophobic core, a kind of "core-shell" formed by self-assembly of hydrophilic chain and hydrophobic chain under molecular force structure. Polymeric drug carriers have some unique properties, such as enhanced water solubility, prolonged circulation time, improved selectivity at tumor sites, and reduced systemic toxicity. However, polymer nano-drug carriers also have shortcomings. Too fast release of the drug before reaching the tumor site can lead to toxic side ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F293/00A61K47/32
Inventor 袁建超慕燕琼赵杰许卫兵陈静静
Owner NORTHWEST NORMAL UNIVERSITY
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